Anthranilamide → Urea

HRID 1292855Notes

Reaction equation

HRID 1292855 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C[N:12]1[C:16](=[O:17])CCC1>>[NH:1]1[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[NH:6][C:16]1=[O:17].[NH2:12][C:4]([NH2:6])=[O:5]

Participants

4

Reactant 2

HCID 6942AnthranilamideHCID 13387N-methyl-2-pyrrolidone

Product 2

HCID 1176UreaHCID 64048Quinazolinedione

Procedure

Amino-benzamide (6) can be cyclized to provide quinazoline-2,4-dione (7) upon treatment with urea in solvent such as NMP. Compound (7) can be treated with N,N-diethylaniline and POCl3 to give 2,4-dichloroquinazoline (8), which, when treated with NH3 in a solvent such as MeOH provides compound (9). Compound (9) can be reacted with t-butyl nitrite in THF to provide compound (10) which, when coupled with an appropriate amine NH2Q, e.g., in NMP, affords compounds of Formula (I).

Sources & evidence

ORD record
ord-485a5c2f6a1b41e0bd1d08d50542fecf
Source dataset
uspto-grants-2007_07
Patent number
US07238698B2

Reaction notes

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